Fluorosilicon nitrile compounds

ABSTRACT

Novel fluorosilicon nitrile compounds, and methods of preparing them, are described. The fluorosilicon nitrile compounds are characterized by having a total of four substituents attached to a silicon atom, wherein one or two of the substituents are fluorine atoms, one or two of the substituents are cyanoalkyl groups, which are the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other.

This present application is the divisional of prior U.S. application Ser. No. 15/506,330 filed Feb. 24, 2017 which was a national phase under 35 USC § 371 of prior PCT International Application Number PCT/US2015/045599 filed Aug. 18, 2015 which designated the United States of America and claimed priority to U.S. Provisional Patent Application Ser. No. 62/042,292 filed Aug. 27, 2014.

FIELD OF THE INVENTION

The present invention pertains to novel fluorosilicon nitrile compounds and methods for their preparation.

DISCUSSION OF THE RELATED ART

Fluorosilicon nitrite compounds containing one or two fluorine atoms attached to a silicon atom as well as at least one cyanoalkyl group attached to the silicon atom may be used in applications such as battery fabrication (as solvents or additives, for example), semiconductor deposition, fluorosilicone glass formation, and semiconductor etching agents. The synthesis of new fluorosilicon compounds of this type would therefore be of great interest, since such new compounds may have unique and varied properties as compared to known fluorosilicon nitrile compounds.

BRIEF SUMMARY OF THE INVENTION

One aspect of the present invention provides novel fluorosilicon nitrile compounds, wherein the fluorosilicon nitrile compound has a total of four substituents attached to a silicon atom and wherein one or two of the substituents are fluorine atoms, one or two of the substituents are cyanoalkyl groups, which are the same as or different from each other (when two cyanoalkyl groups are present), and the remainder of the four substituents, if any, are alkyl groups, which are the same as or different from each other (when two alkyl groups are present); subject to the proviso that the fluorosilicon nitrile compound is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN); SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂.

Also provided by the present invention are fluorosilicon nitrite compounds of general formula Si(R¹)(R²)(R³)(R⁴), wherein one or two of R¹-R⁴ are fluorine atoms, one or two of R¹-R⁴ are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R¹-R⁴, if any, are alkyl groups; subject to the proviso that the fluorosilicon nitrile compound is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN); SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂.

In another aspect of the invention, a method of making a fluorosilicon nitrite compound in accordance with the foregoing description is provided, wherein the method comprises reacting a chlorosilicon nitrile compound, the chlorosilicon nitrite compound having a total of four substituents attached to a silicon atom, wherein one or two of the substituents are chlorine atoms, one or two of the substituents are cyanoalkyl groups, which may be the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other, with a fluorinating agent under conditions effective to exchange fluorine atoms for the chlorine atom(s) in the chlorosilicon nitrile compound.

Still another aspect of the invention provides a method of making a fluorosilicon nitrite compound in accordance with the foregoing description, wherein the method comprises hydrosilylation of an alkene, especially a cyanoalkene, with a fluoroalkylsilane.

DETAILED DESCRIPTION OF CERTAIN EMBODIMENTS OF THE INVENTION

A fluorosilicon nitrite compound in accordance with the present invention has a total of four substituents attached to a silicon atom, wherein one or two of the substituents are fluorine atoms, one or two of the substituents are cyanoalkyl groups, which are the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other. However, the following fluorosilicon nitrite compounds, which are known compounds, are not considered to be within the scope of the present invention: SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN); SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); and SiF₂[CH₂CH(CH₃)CH₂CN]₂.

In one embodiment of the invention, one substituent attached to the silicon atom is a fluorine atom, one substituent is a cyanoalkyl group, and two substituents are alkyl groups, which are the same as or different from each other.

In another embodiment of the invention, two substituents attached to the silicon atom are fluorine atoms, one substituent is a cyanoalkyl group, and one substituent is an alkyl group.

According to another embodiment, one substituent attached to the silicon atom is a fluorine atom, two substituents are cyanoalkyl groups, which are the same as or different from each other, and one substituent is an alkyl group.

In still another embodiment of the invention, two substituents attached to the silicon atom are fluorine atoms and two substituents are cyanoalkyl groups, which are the same as or different from each other.

The cyanoalkyl group or groups attached to the silicon atom may be C2-C9 cyanoalkyl groups, in one aspect of the invention. If two cyanoalkyl groups are present, they may be the same as or different from each other. The alkyl radical bearing one or more cyano (—CN) groups in the cyanoalkyl group may be a straight chain, branched, or alicyclic-containing alkyl radical. Each cyanoalkyl group may contain one, two or more cyano groups per cyanoalkyl group. Each cyano group may be substituted, for example, at a terminal position of an alkyl radical or at an internal position of an alkyl radical. For example, where the alkyl radical is a straight chain C4 alkyl radical, a cyano group may be substituted at the terminal position to provide the cyanoalkyl group —CH₂CH₂CH₂CH₂CN or at an internal position to provide one of the following cyanoalkyl groups: —CH(CN)CH₂CH₂CH₃; —CH₂CH(CN)CH₂CH₃; —CH₂CH₂CH(CN)CH₃.

Suitable cyanoalkyl groups may, for example, be selected from the group consisting of:

-   -   —CH₂CH(CN)CH₃;     -   —CH(CN)CH₂CH₃;     -   —C(CN)(CH₃)₂;     -   —CH₂CH₂CN;     -   —CH(CN)CH₃;     -   —CH₂CH₂CH(CN)CH₃;     -   —CH₂CH(CN)CH₂CH₃;     -   —(CH₂)₃CN;     -   —(CH₂)₂CN;     -   —(CH₂)₄CN;     -   —(CH₂)₅CN;     -   —(CH₂)₃C(CH₃)₂CN;     -   —CH(CH₃)CH₂CN;     -   —CH(CN)CH(CN)CH₃;     -   —C(CN)(CH₃)CH₂CN;     -   —CH(CH₂CN)₂;     -   —CH(CN)CH₂CH₂CN;     -   —CH(CH₃)CH(CN)₂;     -   —C(CN)₂(CH₂CH₃);     -   —CH₂CH(CN)CH₂CN;     -   —C(CN)(CH₃)CH₂CN;     -   —CH(CH₂CH₃)CH₂CN;     -   —CH(CN)CH₂CH₂CH₃;     -   —CH(CH₃)CH₂CH₂CN;     -   —CH(CH₂CN)CH₂CH₃;     -   —CH(CH₃)CH(CH)CH₃;     -   —C(CN)(CH₃)CH₂CH₃;     -   —CH₂CH(CN)CH₂CH₃;     -   —CH₂CH(CH₃)CH₂CN;     -   —C(CH₃)₂CH₂CN;     -   —CH(CN)CH(CH₃)₂;     -   —CH₂CH₂CH(CN)CH₃;     -   —CH₂CH(CH₂CN)CH₂CH₃;     -   —C(CH₃)(CH₂CH₃)CH₂CN;     -   —CH₂CH₂CH(CN)CH₂CH₃;     -   —CH(CH₃)CH(CN)CH₂CH₃;     -   —CH₂CH₂CH₂CH(CN)CH₃;     -   —CH(CH₃)CH₂CH(CN)CH₃;     -   —C(CH₂CH₃)₂(CN);     -   —CH₂CH₂CH(CH₃)CH₂CN;     -   —CH(CH₃)CH(CH₃)CH₂CN;     -   —(CH₂)₂C(CH₃)₂CN;     -   —CH(CH₃)C(CH₃)₂CN;     -   —CH(CH₂CH₃)CH(CN)CH₃;     -   —CH₂CH(CH₃)CH₂CH₂CN;     -   —C(CH₃)₂CH₂CH₂CN;     -   —CH(CH₂CH₃)CH₂CH₂CN;     -   —CH(CH₂CN)CH₂CH₂CH₃;     -   —CH(CN)CH₂CH₂CH₂CH₃;     -   —CH(CH₃)CH₂CH₂CH₂CN;     -   —C(CH₃)₂CH(CN)CH₃;     -   —C(CH₃)(CN)CH(CH₃)₂;     -   —CH(CH₂CN)CH(CH₃)₂;     -   —CH₂CH(CN)CH₂CH₂CH₃;     -   —C(CH₃)(CN)CH₂CH₂CH₃;     -   —CH₂CH(CN)CH(CH₃)₂;     -   —CH(CN)CH₂CH₂CH₂CH₃;     -   —CH₂CH(CH₃)CH(CN)CH₃;     -   —CH(CN)CH₂CH(CH₃)₂;     -   —CH(CN)CH(CH₃)CH₂CH₃;     -   —C(CH₃)(CN)CH(CN)CH₂CH₃;     -   —C(CN)(CH₂CH₃)CH(CN)CH₃;     -   —CH(CH₂CN)CH₂CH₂CH₂CN;     -   —CH(CN)CH₂CH₂CH₂CH₂CN;     -   —CH₂CH(CN)CH₂CH₂CH₂CN;     -   —C(CH₃)(CN)CH₂CH₂CH₂CN;     -   —C(CH₃)(CH₂CH₃)CH(CN)₂;     -   —C(CN)₂CH(CH₃)CH₂CH₃;     -   —C(CN)₂CH₂CH(CH₃)₂;     -   —CH(CH(CN)₂)CH(CH₃)₂;     -   —C(CN)(CH₂CH₃)CH₂CH₂CN;     -   —CH(CH₃)CH(CN)CH₂CH₂CN;     -   —CH₂CH(CN)CH₂CH(CN)CH₃;     -   —C(CN)(CH₃)CH₂CH(CN)CH₃;     -   —(CH₂)₃CH(CN)CH₂CN;     -   —CH(CH₃)CH₂CH(CN)CH₂CN;     -   —CH(CH₂CH₃)CH(CN)CH₂CN;     -   —C(CN)(CH₂CN)CH₂CH₂CH₃;     -   —C(CH₃)₂CH(CN)CH₂CN;     -   —C(CN)(CH₂CN)CH(CH₃)₂;     -   —C(CH₃)(CH₂CN)CH₂CH₂CN;     -   —CH(CH₂CN)CH(CH₃)CH₂CN;     -   —CH₂CH(CH₂CN)CH₂CH₂CN;     -   —CH₂CH(CH₂CN)CH(CN)CH₃;     -   —C(CH₃)(CH₂CN)CH(CN)CH₃;     -   —CH(CH(CN)₂)CH₂CH₂CH₃;     -   —C(CN)₂CH₂CH₂CH₂CH₃;     -   —CH(CH₂CN)CH₂CH(CN)CH₃;     -   —CH(CH₂CH₂CN)CH(CN)CH₃;     -   —CH(CH₃)CH₂CH₂CH(CN)₂;     -   —CH(CH₂CH₃)CH₂CH(CN)₂;     -   —CH₂CH(CH₃)CH₂CH(CN)₂;     -   —C(CH₃)₂CH₂CH(CN)₂;     -   —CH₂CH₂CH₂C(CN)₂CH₃;     -   —CH(CH₃)CH₂C(CN)₂CH₃;     -   —CH(CH(CN)₂)CH(CH₃)₂;     -   —CH₂CH₂CH(CH₃)CH(CN)₂;     -   —CH(CH₃)CH(CH₃)CH(CN)₂; and     -   —CH₂CH₂CH₂CH₂CH(CN)₂ and combinations thereof, where the         fluorosilicon nitrile compound contains two cyanoalkyl groups         per molecule.

When at least one alkyl group is present in the fluorosilicon nitrile compound as a substituent attached to the silicon atom, the alkyl group may, for example, be a C1-C8 alkyl group. The alkyl group may be straight chain or branched or may contain a cyclic structure (i.e., the alkyl group may be alicyclic). If two alkyl groups are attached to the silicon atom, they may be the same as each other or different from each other. Suitable alkyl groups include, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, and n-octyl and isomers thereof.

In one aspect of the invention, the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, one fluorine atom, one cyanoalkyl group, and two C1-C8 alkyl groups, which are the same as or different from each other. In another aspect of the invention, the fluorosilicon nitrile compound contains, as substituents attached to the silicon atom, two fluorine atoms, one cyanoalkyl group and one C1-C8 alkyl group. In these embodiments, the C1-C8 alkyl groups may, for example, be selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and combinations thereof.

A further embodiment of the invention provides a fluorosilicon nitrile compound of general formula Si(R¹)(R²)(R³)(R⁴), wherein one or two of R¹-R⁴ are fluorine atoms, one or two of R¹-R⁴ are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R¹-R⁴, if any, are alkyl groups; subject to the proviso that the fluorosilicon nitrile compound is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃); SiF₂(CH₃)(CH₂CH₂CH₂CN); SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂. The alkyl groups and cyanoalkyl groups may be any of such groups described previously.

For example, R¹ and R² may both be F, R³ may be an alkyl group and R⁴ may be a cyanoalkyl group. Alternatively, R¹ and R² may both be F and R³ and R⁴ may both be cyanoalkyl groups. In yet another aspect, R1 may be F, R² and R³ may both be alkyl, and R⁴ may be cyanoalkyl. Additionally, in a further aspect of the invention, R¹ may be F, R² may be alkyl, and R³ and R⁴ may both be cyanoalkyl.

Examples of fluorosilicon nitrile compounds in accordance with the present invention are shown in Table I. Each of these compounds may be synthesized from known chlorosilicon nitrile compounds containing Cl atoms, rather than F atoms, substituted on the silicon atom, using the fluorination methods described elsewhere herein.

TABLE I Empirical Compound # Structure Formula  1

C₆H₁₂NSiF  2

C₅H₉NSiF₂  3

C₅H₉NSiF₂  4

C₅H₉NSiF₂  5

C₅H₉NSiF₂  6

C₇H₁₄NSiF  7

C₇H₁₄NSiF  8

C₇H₁₄NSiF  9

C₈H₁₂N₂SiF₂ 10

C₇H₁₁N₂SiF 11

C₇H₁₁N₂SiF 12

C₆H₈N₂SiF₂ 13

C₉H₁₈NSiF 14

C₈H₁₅NSiF₂ 15

C₁₀H₂₀NSiF 16

C₆H₁₁NSiF₂

Additional exemplary fluorosilicon nitrile compounds illustrative of the present invention are shown in Table II. These compounds contain one or two fluorine atoms attached to a silicon atom, a cyanoalkyl group attached to the silicon atom, and one or two methyl groups attached to the silicon atom. Also within the scope of the present invention are fluorosilicon compounds homologous or analogous to those shown in Table II in which the methyl group (in the case of the difluoromethylsilicon nitriles) or one or both of the methyl groups (in the case of the fluorodimethylsilicon nitriles) is or are substituted by an alkyl group other than methyl, in particular a branched or straight chain C2-C8 alkyl group such as ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and the like.

TABLE II Compound Fluorodimethylsilicon Difluoromethylsilicon # Nitrile Nitrile 21

21a = C₆H₁₂NSiF 21b = C₅H₉NSiF₂

21c = C₆H₁₂NSiF 21d = C₅H₉NSiF₂ 22

22a =C₇H₁₁N₂SiF 22b = C₆H₈N₂SiF₂

22c = C₇H₁₁N₂SiF 22d = C₆H₈N₂SiF₂ 23

23a = C₇H₁₁N₂SiF 23b = C₆H₈N₂SiF₂

23c = C₇H₁₁N₂SiF 23d =C₆H₈N₂SiF₂ 24

24a = C₇H₁₁N₂SiF 24b = C₆H₈N₂SiF₂

24c = C₇H₁₁N₂SiF 24d = C₆H₈N₂SiF₂ 25

25a = C₇H₁₁N₂SiF 25b = C₆H₈N₂SiF₂

25c = C₇H₁₁N₂SiF 25d = C₆H₈N₂SiF₂ 26

26a = C₇H₁₄NSiF 26b = C₆H₁₁NSiF₂

26c = C₇H₁₄NSiF 26d = C₆H₁₁NSiF₂ 27

27a = C₇H₁₄NSiF 27b = C₆H₁₁NSiF₂

27c = C₇H₁₄NSiF 27d = C₆H₁₁NSiF₂ 28

28a = C₇H₁₄NSiF 28b = C₆H₁₁NSiF₂

28c = C₇H₁₄NSiF 28d = C₆H₁₁NSiF₂ 29

29a = C₇H₁₄NSiF 29b = C₆H₁₁NSiF₂

29c = C₇H₁₄NSiF 29d = C₆H₁₁NSiF₂ 30

30a = C₇H₁₄NSiF 30b = C₆H₁₁NSiF₂ 31

31a = C₇H₁₄NSiF

31b = C₇H₁₄NSiF 31c = C₆H₁₁NSiF₂ 32

32a = C₇H₁₄NSiF 32b = C₆H₁₁NSiF₂ 33

33 = C₇H₁₄NSiF 34

34a = C₈H₁₆NSiF 34b = C₇H₁₃NSiF₂

34c = C₈H₁₆NSiF 34d = C₇H₁₃NSiF₂ 35

35a = C₈H₁₆NSiF 35b = C₇H₁₃NSiF₂

35c = C₈H₁₆NSiF 35d = C₇H₁₃NSiF₂ 36

36a = C₈H₁₆NSiF 36b = C₇H₁₃NSiF₂

36c = C₈H₁₆NSiF 36d = C₇H₁₃NSiF₂ 37

37a = C₈H₁₆NSIF 37b = C₇H₁₃NSiF₂ 38

38a = C₈H₁₆NSiF 38b = C₇H₁₃NSiF₂

38c = C₈H₁₆NSiF 38d = C₇H₁₃NSiF₂ 39

39a = C₈H₁₆NSiF 39b = C₇H₁₃NSiF₂

39c = C₈H₁₆NSiF 39d = C₇H₁₃NSiF₂ 40

40a = C₈H₁₆NSiF 40b = C₇H₁₃NSiF₂ 41

41a = C₈H₁₆NSiF 41b = C₇H₁₃NSiF₂

41c = C₈H₁₆NSiF 41d = C₇H₁₃NSiF₂ 42

42a = C₈H₁₆NSiF 42b = C₇H₁₃NSiF₂

42c = C₈H₁₆NSiF 42d = C₇H₁₃NSiF₂ 43

43a = C₈H₁₆NSiF 43b = C₇H₁₃NSiF₂ 44

44a = C₈H₁₆NSiF 44b = C₇H₁₃NSiF₂

44c = C₈H₁₆NSiF 44d = C₇H₁₃NSiF₂ 45

45a = C₈H₁₆NSiF 45b = C₇H₁₃NSiF₂

45c = C₈H₁₆NSiF 45d = C₇H₁₃NSiF₂ 46

46a = C₈H₁₆NSiF 46b = C₇H₁₃NSiF₂ 47

47a = C₈H₁₆NSiF 47b = C₇H₁₃NSiF₂

47c = C₈H₁₆NSiF 47d = C₇H₁₃NSiF₂ 48

48a = C₈H₁₆NSiF 48b = C₇H₁₃NSiF₂ 49

49a = C₈H₁₆NSiF 49b = C₇H₁₃NSiF₂ 50

50a = C₈H₁₆NSiF 50b = C₇H₁₃NSiF₂ 51

51a = C₈H₁₆NSiF 51b = C₇H₁₃NSiF₂ 52

52a = C₈H₁₆NSiF 52b = C₇H₁₃NSiF₂ 53

53a = C₉H₁₅N₂SiF 53b = C₈H₁₂N₂SiF₂

53c = C₉H₁₅N₂SiF 53d = C₈H₁₂N₂SiF₂ 54

54a = C₉H₁₅N₂SiF 54b = C₈H₁₂N₂SiF₂

54c = C₉H₁₅N₂SiF 54d = C₈H₁₂N₂SiF₂ 55

55a = C₉H₁₅N₂SiF 55b = C₈H₁₂N₂SiF₂

55c = C₉H₁₅N₂SiF 55d = C₈H₁₂N₂SiF₂ 56

56a = C₉H₁₅N₂SiF 56b = C₈H₁₂N₂SiF₂

56c = C₉H₁₅N₂SiF 56d = C₈H₁₂N₂SiF₂ 57

57a = C₉H₁₅N₂SiF 57b = C₈H₁₂N₂SiF₂

57c = C₉H₁₅N₂SiF 57d = C₈H₁₂N₂SiF₂ 58

58a = C₉H₁₅N₂SiF 58b = C₈H₁₂N₂SiF₂

58c = C₉H₁₅N₂SiF 58d = C₈H₁₂N₂SiF₂ 59

59a = C₉H₁₅N₂SiF 59b = C₈H₁₂N₂SiF₂

59c = C₉H₁₅N₂SiF 59d = C₈H₁₂N₂SiF₂ 60

60a = C₉H₁₅N₂SiF 60b = C₈H₁₂N₂SiF₂

60c = C₉H₁₅N₂SiF 60d = C₈H₁₂N₂SiF₂ 61

61a = C₉H₁₅N₂SiF 61b = C₈H₁₂N₂SiF₂ 62

62a = C₉H₁₅N₂SiF 62b = C₈H₁₂N₂SiF₂ 63

63a = C₉H₁₅N₂SiF 63b = C₈H₁₂N₂SiF₂

63c = C₉H₁₅N₂SiF 63d = C₈H₁₂N₂SiF₂ 64

64a = C₉H₁₅N₂SiF 64b = C₈H₁₂N₂SiF₂

64c = C₉H₁₅N₂SiF 64d = C₈H₁₂N₂SiF₂ 65

65a = C₉H₁₅N₂SiF 65b = C₈H₁₂N₂SiF₂ 66

66a = C₉H₁₅N₂SiF 66b = C₈H₁₂N₂SiF₂

66c = C₉H₁₅N₂SiF 66d = C₈H₁₂N₂SiF₂ 67

67a = C₉H₁₅N₂SiF 67b = C₈H₁₂N₂SiF₂

67c = C₉H₁₅N₂SiF 67d = C₈H₁₂N₂SiF₂ 68

681 = C₉H₁₅N₂SiF 68b = C₈H₁₂N₂SiF₂

68c = C₉H₁₅N₂SiF 68d = C₈H₁₂N₂SiF₂ 69

69a = C₉H₁₅N₂SiF 69b = C₈H₁₂N₂SiF₂

69c = C₉H₁₅N₂SiF 69d = C₈H₁₂N₂SiF₂ 70

70a = C₉H₁₅N₂SiF 70b = C₈H₁₂N₂SiF₂

70c = C₉H₁₅N₂SiF 70d = C₈H₁₂N₂SiF₂ 71

71a = C₉H₁₅N₂SiF 71b = C₈H₁₂N₂SiF₂

71c = C₉H₁₅N₂SiF 71d = C₈H₁₂N₂SiF₂ 72

72a = C₉H₁₅N₂SiF 72b = C₈H₁₂N₂SiF₂ 73

73a = C₉H₁₅N₂SiF 73b = C₈H₁₂N₂SiF₂

73c = C₉H₁₅N₂SiF 73d = C₈H₁₂N₂SiF₂ 74

74a = C₉H₁₅N₂SiF 74b = C₈H₁₂N₂SiF₂

Also provided by the present invention are methods of making the above-mentioned fluorosilicon nitrile compounds.

In one aspect of the invention, a method is provided which comprises reacting a chlorosilicon nitrile compound with a fluorinating agent under conditions effective to exchange fluorine atoms for the chlorine atoms in the chlorosilicon nitrile compound. The chlorosilicon nitrile compound has a total of four substituents attached to a silicon atom, wherein one or two of the substituents are chlorine atoms, one or two of the substituents are cyanoalkyl groups, which may be the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other. The chlorosilicon nitrile compound may correspond to general formula Si(R¹)(R²)(R³)(R⁴), wherein one or two of R¹-R⁴ are chlorine atoms, one or two of R¹-R⁴ are cyanoalkyl groups, which are the same as or different from each other where two cyanoalkyl groups are present, and the remaining R¹-R⁴, if any, are alkyl groups.

The fluorinating agent may, for example, be selected from the group consisting of HF, MF, MHF₂ and SbF₃, where M is Na, K, Rb, Cs or NH₄. Fluorides of antimony, zinc, lead, mercury, silver, cobalt, copper, tungsten and other metals may be utilized as the fluorinating agent. Sodium fluoroborate may also he used, as can mixtures of SbF₃ and BF₃ or NaF and sulfuric acid. Other suitable fluorinating agents include neat BF₃, BF₃ etherates, Na₂SiF₆, NaPF₆, NaSbF₆, NaBF₄, Me₃SnF, PF₅, PhCBF₄, NOBF₄, and NO₂BF₄. If HF (hydrogen fluoride) is employed, it may be used in anhydrous form or in an aqueous-alcoholic or aqueous medium. Potassium hydrogen difluoride and ammonium hydrogen difluoride (ammonium bifluoride) are especially useful fluorinating agents.

Certain of the chlorosilicon nitrile compounds useful as the starting material in the aforementioned fluorination reaction are known compounds that may be prepared using methods known in the art. Such compounds include, for example, compounds having the following CAS registration numbers: 42759-42-2; 59343-99-6; 42759-43-3; 100792-00-5, 1068-40-2; 18243-57-7; 1274903-71-7, 876343-97-4; 2617-09-6; 18276-25-0; 18135-77-8; 103613-06-5; 1071-17-6; 18727-31-6; 7031-17-6; 169206-21-7; 875478-07-2; 161582-95-2; 113641-37-5; and 1186-40-9. Additional chlorosilicon nitrile compounds may be readily synthesized by hydrosilylation of an alkene with a chloroalkylsilane. In one embodiment of such a synthesis, the alkene is a cyanoalkene. The cyanoalkene may suitably be a C3-C10 cyanoalkene, for example, and may contain a single carbon-carbon double bond and one, two or more cyano (—CN) groups per molecule. The structure of the cyanoalkene is selected so as to provide a cyanoalkyl group of the type desired in the fluorosilicon nitrile produced by hydrosilylation. Illustrative examples of suitable cyanoalkenes include, but are not limited to, CH₃CH═CHCN (CAS 4786-20-3); CH₃C(CN)═CHCN (CAS 70240-55-0); NCCH₂CH═CHCN (CAS 7717-24-0); CH₃CH═C(CN)₂ (CAS 1508-07-2); CH₂═C(CN)CH₂CN (CAS 24412-94-0); CH₃CH₂CH═CHCN (CAS 13284-42-9); CH₂═CHCH₂CH₂CN (CAS 592-51-8); CH₃CH═CHCH₂CN (CAS 4635-87-4); CH₃CH═C(CN)CH₃ (CAS 4403-61-6); CH₂═C(CN)CH₂CH₃ (CAS 1647-11-6); CH₂═C(CH₃)CH₂CN (CAS 4786-19-0); (CH₃)₂C═CHCN (CAS 4786-24-7); CH₂CHCH(CN)CH₃ (CAS 16529-56-9); CH₂═C(CH₂CN)CH₂CH₃ (CAS 1462956-36-0); CH₂═CHCH(CN)CH₂CH₃ (CAS 180974-28-1); CH₂═CHCH₂CH(CN)CH₃ (CAS 89464-18-6); CH₃CH₂C(CN)═CHCH₃ (CAS 89580-25-6); CH₂CHCH(CH₃)CH₂CN (CAS 51980-04-2); CH₂═CHC(CH₃)₂CN (CAS 41405-16-7); CH₃CH(CN)CH═CHCH₃ (CAS 37674-624); CH₂═C(CH₃)CH₂CH₂CN (CAS 34998-36-2); CH₃CH₂CH═CHCH₂CN (CAS 16170-44-8); CH₃CH₂CH₂CH═CHCN (CAS 5636-69-1); CH₂═CHCH₂CH₂CH₂CN (CAS 5048-19-1); (CH₃)₂C═C(CH₃)CN (CAS 4786-37-2); (CH₃)₂C═CHCH₂CN (CAS 4786-23-6); CH₂═C(CN)CH₂CH₂CH₃ (CAS 3931-57-5); CH₂═C(CN)CH(CH₃)₂ (CAS 2813-69-6); CH₃CH₂CH₂CH═CHCN (CAS 67889-07-0); CH₂C(CH₃)CH(CN)CH₃ (CAS 25653-08-1); (CH₃)₂CHCH═CHCN (CAS 19124-15-3); CH₃CH₂C(CH₃)═CHCN (CAS 14799-77-0); CH₃C(CN)═C(CN)CH₂CH₃ (CAS 1003003-54-0); NCCH₂CH₂CH₂CH═CHCN (CAS 872307-67-0); CH₂═C(CN)CH₂CH₂CH₂CN (CAS 856347-40-5); CH₃CH₂C(CH₃)═C(CN)₂ (CAS 13017-50-0); (CH₃)₂CHCH═C(CN)₂ (CAS 13134-03-7); CH₃CH═C(CN)CH₂CH₂CN (CAS 22485-88-7); CH₂═C(CN)CH₂CH(CN)CH₃ (CAS 35299-21-9); CH₂═CHCH₂CH(CN)CH₂CN (CAS 364453-09-5); CH₃CH═CHCH(CN)CH₂CN (CAS 36453-10-8); CH₃CH₂CH═C(CN)CH₂CN (CAS 36453-11-9); (CH₃)₂C═C(CN)CH₂CN (CAS 67386-03-2); NCCH₂C(CH₃)═CHCH₂CN (CAS 76257-96-0); CH₂═C(CH₂CN)CH₂CH₂CN (CAS 80718-20-3); CH₂═C(CH₂CN)CH(CN)CH₃ (CAS 80718-26-9); CH₃CH₂CH₂CH═C(CN)₂ (CAS 87948-15-0); CH₃CH(CN)CH═CHCH₂CN (CAS 122917-04-8); (NC)₂CHCH₂CH═CHCH₃ (CAS 130575-29-0); CH₂═C(CH₃)CH₂CH(CN)₂ (CAS 145050-18-6); CH₂═CHCH₂C(CN)₂CH₃ (CAS 154657-02-0); (CH₃)₂C═CHCH(CN)₂ (CAS 442661-894); CH₂═CHCH(CH₃)CH(CN)₂ (CAS 443124-95-6); and CH₂═CHCH₂CH₂CH(CN)₂ (CAS 475197-78-5).

The chloroalkylsilane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, one chlorine atom and one or two alkyl groups, which may be the same as each other or different from each other. Where one hydrogen atom is present, one molecule of cyanoalkene reacts with one molecule of chloroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms are present, two molecules of cyanoalkene react with one molecule of chloroalkylsilane, thereby introducing two cyanoalkyl groups into the silane. In this embodiment, the chloroalkyl silane may correspond to the general structure SiCl(H)_(m)(R)_(3-n), where n is 1 or 2 and R is alkyl. In another aspect of the invention, the chloroalkyl silane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, two chlorine atoms, and, where only one hydrogen atom is attached to silicon, a single alkyl group. In this embodiment, the chloroalkyl silane may correspond to the general structure SiCl₂(H)_(n)(R)_(2-n), where n is 1 or 2 and R, if present, is alkyl. Where one hydrogen atom is present, one molecule of cyanoalkene reacts with one molecule of ehloroalkylsitane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms are present, two molecules of alkene react with one molecule of chloroalkylsilane, thereby introducing two cyanoalkyl groups into the silane.

The alkyl groups may, for example, be a C1-C8 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl and isomers thereof, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-octyl and isomers thereof and combinations of such alkyl groups. The chloroalkylsilane thus may correspond to the general formula HSi(R¹)(R²)(R³), wherein one or two of R¹-R³ are chlorine atoms and the remaining R¹-R³ are alkyl groups, which may be the same as or different from each other where more than one alkyl group per molecule is present.

An example of such a synthetic reaction scheme is shown below. In this example, the alkene 2-cyanobut-1-ene (CAS #1647-11-6) is hydrosilylated with chlorodimethylsilane (CDMS), leading to a chlorosilicon nitrite having the structure shown (Reaction 1A). The chlorosilicon nitrite is then reacted with a fluorinating agent to produce fluorosilicon nitrite compound 30a having the structure shown (Reaction 1B).

A further method of making a fluorosilicon nitrite compound in accordance with the present invention comprises hydrosilylation of an alkene with a fluoroalkylsilane (i.e., reacting the alkene and fluoroalkylsilane under hydrosilylation conditions). The reacted alkene may be a cyanoalkene, for example. Suitable cyanoalkenes include any of the previously mentioned cyanoalkenes.

The fluoroalkylsilane may be a silane containing, as substituents attached to the silicon atom, one or two hydrogen atoms, one fluorine atom and one or two alkyl groups, which may be the same as each other or different from each other. The total number of hydrogen atoms, fluorine atom, and alkyl groups equals four. Where one hydrogen atom attached to silicon is present, one molecule of cyanoalkene reacts with one molecule of fluoroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms attached to silicon are present, two molecules of cyanoalkene react with one molecule of fluoroalkylsilane, thereby introducing two cyanoalkyl groups into the silane. In this embodiment, the fluoroalkyl silane may correspond to the general structure SiF(H)_(n)(R)^(3-n), where n is 1 or 2 and R is alkyl. In another aspect of the invention, the fluoroalkyl silane may be a slime containing, as substituents attached to the silicon atom, one or two hydrogen atoms, two fluorine atoms, and, where only one hydrogen atom is attached to silicon, a single alkyl group. The total number of hydrogen atoms, fluorine atoms and alkyl group equals four. In this embodiment, the fluoroalkyl silane may correspond to the general structure SiF₂(H)_(n)(R)_(2-n), where n is 1 or 2 and R, if present, is alkyl. Where one hydrogen atom attached to silicon is present, one molecule of cyanoalkene reacts with one molecule of fluoroalkylsilane in the hydrosilylation reaction, thereby introducing a single cyanoalkyl group into the silane. When two hydrogen atoms attached to silicon are present, two molecules of cyanoalkene react with one molecule of fluoroalkylsilane, thereby introducing two cyanoalkyl groups into the silane.

The alkyl groups may, for example, be a C1-C8 alkyl group such as methyl, ethyl, n-propyl, isopropyl, n-butyl and isomers thereof, n-pentyl and isomers thereof, n-hexyl and isomers thereof, n-heptyl and isomers thereof, n-octyl and isomers thereof and combinations of such alkyl groups.

The fluoroalkylsilane thus may correspond to the general formula HSi(R¹)(R²)(R³), wherein one or two of R¹-R³ are fluorine atoms and the remaining R¹-R³ are alkyl groups, which may be the same as or different from each other where more than one alkyl group per molecule is present.

The following reaction scheme (Reaction 1C) is an example of such a reaction. In this example, fluorosilicon nitrile compound 30a is prepared by direct hydrosilylation of the alkene 2-cyanobut-1-ene with fluorodimethylsilane (FDMS).

In one embodiment of the invention, the above-mentioned hydrosilylation reactions are carried out in the presence of a hydrosilylation catalyst, in particular an organoplatinum coordination complex having activity as a hydrosilylation catalyst. Karstedt's catalyst, which is an organoplatinum compound derived from divinyl-containing disiloxane (by treatment of chloroplatinic acid with divinyltetramethyldisiloxane), is an example of a suitable catalyst for this purpose. Other suitable hydrosilylation catalysts include, for example, Wilkinson's catalyst (tris(triphenylphosphone)rhodium (I) chloride), the cobalt carbonyl complex Co₂(CO)₈, and H₂PtCl₆(Speier's catalyst). Hydrosilylation typically proceeds in an anti-Markovnikov manner. However, depending upon the reaction conditions used, hydrosilylation may not be completely selective; that is, a mixture of isomeric hydrosilylation products may be obtained. The individual components of such reaction product mixtures may be purified and isolated using any conventionally known techniques, such as fractional distillation. Alternatively, the mixture of components may be utilized for the desired end use without such fractionation or separation.

Typically, where it is desired to introduce a single cyanoalkyl group into a silane, the molar ratio of cyanoalkene to fluoroalkylsilane may be approximately 1:1, e.g., from about 0.7:1 to about 1.3:1. If it is desired to introduce two cyanoalkyl groups, the molar ratio of cyanoalkene to fluoroalkylsilane may be approximately 2:1, e.g., from about 1.5:1 to about 15:1. The hydrosilylation may be carried out using an organic solvent, e.g., an aromatic hydrocarbon, as a reaction medium. The mixture of cyanoalkene, fluoroalkylsilane, hydrosilylation catalyst and optional solvent may be heated for a time and at a temperature effective to provide the desired conversion of the starting materials. For example, reaction temperatures of from about 50° C. to about 110° C. and reaction times of from about 1 to about 6 hours may be utilized.

Aspects of the present invention include:

-   -   1. A fluorosilicon nitrile compound having a total of four         substituents attached to a silicon atom, wherein one or two of         the substituents are fluorine atoms, one or two of the         substituents are cyanoalkyl groups, which are the same as or         different from each other, and the remainder of the         substituents, if any, are alkyl groups, which are the same as or         different from each other;         -   subject to the proviso that the fluorosilicon nitrile             compound is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃);             SiF₂(CH₃)(CH₂CH₂CH₂CN); SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or             SiF₂[CH₂CH(CH₃)CH₂CN]₂.     -   2. The fluorosilicon nitrile compound of claim 1, wherein one         substitutent is a fluorine atom, one substituent is a cyanoalkyl         group, and two substituents are alkyl groups, which are the same         as or different from each other.     -   3. The fluorosilicon nitrite compound of claim 1, wherein two         substituents are fluorine atoms, one substituent is a cyanoalkyl         group, and one substituent is an alkyl group.     -   4. The fluorosilicon nitrile compound of claim 1, wherein one         substituent is a fluorine atom, two substituents are cyanoalkyl         groups, which are the same as or different from each other, and         one substituent is an alkyl group.     -   5. The fluorosilicon nitrite compound of claim 1, wherein two         substituents are fluorine atoms and two substituents are         cyanoalkyl groups, which are the same as or different from each         other.     -   6. The fluorosilicon nitrite compound of any one of the         preceding claims, wherein the cyanoalkyl groups are C2-C9         cyanoalkyl groups.     -   7. The fluorosilicon nitrile compound of claim 1, wherein at         least one alkyl group is present and the alkyl group is a C1-C8         alkyl group,     -   8. The fluorosilicon nitrite compound of any one of the         preceding claims, wherein the cyanoalkyl group or cyanoalkyl         groups contain(s) a single cyano group per cyanoalkyl group.     -   9. The fluorosilicon nitrite compound of any one of claims 1         through 7, wherein the cyanoalkyl group or cyanoalkyl groups         contain(s) two cyano groups per cyanoalkyl group.     -   10. The fluorosilicon nitrite compound of any one of the         preceding wherein the cyanoalkyl group or cyanoalkyl groups         contain(s) a cyano group which is substituted at a terminal         position of an alkyl radical.     -   11. The fluorosilicon nitrite compound of any one of the         preceding wherein the cyanoalkyl group or cyanoalkyl groups         contain(s) a cyano group which is substituted at an internal         position of an alkyl radical.     -   12. The fluorosilicon nitrile compound of any one of the         preceding claims, wherein the cyanoalkyl group or cyanoalkyl         groups are selected from the group consisting of:         -   —CH₂CH(CN)CH₃;         -   —CH(CN)CH₂CH₃;         -   —C(CN)(CH₃)₂;         -   —CH₂CH₂CN;         -   —CH(CN)CH₃;         -   —CH₂CH₂CH(CN)CH₃;         -   —CH₂CH(CN)CH₂CH₃;         -   —(CH₂)₃CN;         -   —(CH₂)₂CN;         -   —(CH₂)₄CN;         -   —(CH₂)₅CN;         -   —(CH₂)₃C(CN)₂CH₃;         -   —CH(CH₃)CH₂CN;         -   —CH(CN)CH(CN)CH₃;         -   —C(CN)(CH₃)CH₂CN;         -   —CH(CH₂CN)₂;         -   —CH(CN)CH₂CH₂CN;         -   —CH(CH₃)CH(CN)₂;         -   —C(CN)₂(CH₂CH₃);         -   —CH₂CH(CN)CH₂CN;         -   —C(CN)(CH₃)CH₂CN;         -   —CH(CH₂CH₃)CH₂CN;         -   —CH(CN)CH₂CH₂CH₃;         -   —CH(CH₃)CH₂CH₂CN;         -   —CH(CH₂CN)CH₂CH₃;         -   —CH(CH₃)CH(CN)CH₃;         -   —C(CN)(CH₃)CH₂CH₃;         -   —CH₂CH(CH₃)CH₂CN;         -   —C(CH₃)₂CH₂CN;         -   —CH(CN)CH(CH₃)₂;         -   —CH₂CH₂CH(CN)CH₃;         -   —CH₂CH(CH₂CN)CH₂CH₃;         -   —C(CH₃)(CH₂CH₃)CH₂CN;         -   —CH₂CH₂CH(CN)CH₂CH₃;         -   —CH(CH₃)CH(CN)CH₂CH₃;         -   —CH₂CH₂CH₂CH(CN)CH₃;         -   —CH(CH₃)(CH₂CH(CN)CH₃;         -   —C(CH₂CH₃)₂(CN);         -   —CH₂CH₂CH(CH₃)CH₂CN;         -   —CH(CH₃)CH(CH₃)CH₂CN;         -   —(CH₂)₂C(CH₃)₂CN;         -   —CH(CH₃)C(CH₃)₂CN;         -   —CH(CH₂CH₃)CH(CN)CH₃;         -   —CH₂CH(CH₃)CH₂CH₂CN;         -   —C(CH₃)₂CH₂CH₂CN;         -   —CH(CH₂CH₃)CH₂CH₂CN;         -   —CH(CH₂CN)CH₂CH₂CH₃;         -   —CH(CN)CH₂CH₂CH₂CH₃;         -   —CH(CH₃)CH₂CH₂CH₂CN;         -   —C(CH₃)₂CH(CN)CH₃;         -   —C(CH₃)(CN)CH(CH₃)₂;         -   —CH(CH₂CN)CH(CH₃)₂;         -   —CH₂CH(CN)CH₂CH₂CH₃;         -   —C(CH₃(CN)CH₂CH₂CH₃;         -   —CH₂CH(CN)CH(CH₃)₂;         -   —CH(CN)CH₂CH₂CH₂CH₃;         -   —CH₂CH(CH₃)CH(CN)CH₃;         -   —CH(CN)CH₂CH(CH₃)₂;         -   —CH(CN)CH(CH₃)CH₂CH₃;         -   —C(CH₃)(CN)CH(CN)CH₂CH₃;         -   —C(CN)(CH₂CH₃)CH(CN)CH₃;         -   —CH(CH₂CN)CH₂CH₂CH₂CN;         -   —CH(CN)CH₂CH₂CH₂CH₂CN;         -   —CH₂CH(CN)CH₂CH₂CH₂CN;         -   —C(CH₃)(CN)CH₂CH₂CH₂CN;         -   —C(CH₃)(CH₂CH₃)CH(CN)₂;         -   —C(CN)₂CH(CH₃)CH₂CH₃;         -   —C(CN)₂CH₂CH(CH₃)₂;         -   —CH(CH(CN)₂)CH(CH₃)₂;         -   —C(CN)(CH₂CH₃)CH₂CH₂CN;         -   —CH(CH₃)CH(CN)CH₂CH₂CN;         -   —CH₂CH(CN)CH₂CH(CN)CH₃;         -   —C(CN)(CH₃)CH₂CH(CN)CH₃;         -   —(CH₂)₃CH(CN)CH₂CN;         -   —CH(CH₃)CH₂CH(CN)CH₂CN;         -   —CH(CH₂CH₃)CH(CN)CH₂CN;         -   —C(CN)(CH₂CN)CH₂CH₂CH₃;         -   —C(CH₃)₂CH(CN)CH₂CN;         -   —C(CN)(CH₂CN)CH(CH₃)₂;         -   —C(CH₃)(CH₂CN)CH₂CH₂CN;         -   —CH(CH₂CN)CH(CH₃)CH₂CN;         -   —CH₂CH(CH₂CN)CH₂CH₂CN;         -   —CH₂CH(CH₂CN)CH(CN)CH₃;         -   —C(CH₃)(CH₂CN)CH(CN)CH₃;         -   —CH(CH(CN)₂)CH₂CH₂CH₃;         -   —C(CN)₂CH₂CH₂CH₂CH₃;         -   —CH(CH₂CN)CH₂CH(CN)CH₃;         -   —CH(CH₂CH₂CN)CH(CN)CH₃;         -   —CH(CH₃)CH₂CH₂CH(CN)₂;         -   —CH(CH₂CH₃)CH₂CH(CN)₂;         -   —CH₂CH(CH₃)CH₂CH(CN)₂;         -   —C(CH₃)₂CH₂CH(CN)₂;         -   —CH₂CH₂CH₂C(CN)₂CH₃;         -   —CH(CH₃)CH₂C(CN)₂CH₃;         -   —CH(CH(CN)₂)CH(CH₃)₂;         -   —CH₂CH₂CH(CH₃)CH(CN)₂;         -   —CH(CH₃)CH(CH₃)CH(CN)₂; and         -   —CH₂CH₂CH₂CH₂CH(CN)₂ and combinations thereof.     -   13. The fluorosilicon nitrile compound of claim 12, wherein the         fluorosilicon nitrile compound contains, as substituents         attached to the silicon atom, one fluorine atom, one cyanoalkyl         group, and two C1-C8 alkyl groups, which are the same as or         different from each other.     -   14. The fluorosilicon nitrile compound of claim 13, wherein the         fluorosilicon nitrile compound contains, as substituents         attached to the silicon atom, two alkyl groups selected from the         group consisting of methyl, ethyl, n-propyl, iso-propyl,         n-butyl, sec-butyl, iso-butyl, tert-butyl and combinations         thereof.     -   15. The fluorosilicon nitrile compound of claim 12, wherein the         fluorosilicon nitrile compound contains, as substituents         attached to the silicon atom, two fluorine atoms, one cyanoalkyl         group and one C1-C8 alkyl group.     -   16. The fluorosilicon nitrile compound of claim 12 or 15,         wherein the fluorosilicon nitrile compound contains, as         substituents attached to the silicon atom, two alkyl groups         selected from the group consisting of methyl, ethyl, n-propyl,         iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl and         combinations thereof.     -   17. A fluorosilicon nitrile compound of general formula         Si(R¹)(R²)(R³)(R⁴), wherein one or two of R¹-R⁴ are fluorine         atoms, one or two of R¹-R⁴ are cyanoalkyl groups, which are the         same as or different from each other where two cyanoalkyl groups         are present, and the remaining R¹-R⁴, if any, are alkyl groups;         subject to the proviso that the fluorosilicon nitrile compound         is not SiF₂(CH₃)(CH₂CH₂CH(CN)CH₃; SiF₂(CH₃)(CH₂CH₂CH₂CN);         SiF₂(CH₃)(CH₂CH(CH₃)CH₂CN); or SiF₂[CH₂CH(CH₃)CH₂CN]₂.     -   18. A method of making a fluorosilicon nitrile compound in         accordance with any one of the preceding claims, wherein the         method comprises reacting a chlorosilicon nitrile compound with         a fluorinating agent under conditions effective to exchange         fluorine atoms for the chlorine atoms in the chlorosilicon         nitrile compound and wherein the chlorosilicon nitrile compound         has a total of four substituents attached to a silicon atom,         wherein one or two of the substituents are chlorine atoms, one         or two of the substituents are cyanoalkyl groups, which may be         the same as or different from each other, and the remainder of         the substituents, if any, are alkyl groups, which are the same         as or different from each other.     -   19. The method of claim 18, wherein the fluorinating agent is         selected from the group consisting of HF, MF, MHF₂ and SbF₃,         where M is Na, K, Rb, Cs or NH₄.     -   20. The method of claim 18 or 19, wherein the chlorosilicon         nitrile compound is prepared by hydrosilylation of an alkene         with a chloroalkylsilane.     -   21. The method of claims 18 through 20, wherein the alkene is a         cyanoalkene.     -   22. A method of making a fluorosilicon nitrile compound in         accordance with any one of the preceding claims, wherein the         method comprises hydrosilylation of an alkene with a         fluoroalkylsilane.     -   23. The method of claim 22, wherein the alkene is a cyanoalkene.

Within this specification embodiments have been described in a way which enables a clear and concise specification to be written, but it is intended and will be appreciated that embodiments may be variously combined or separated without parting from the invention. For example, it will be appreciated that all preferred features described herein are applicable to all aspects of the invention described herein. 

What is claimed is:
 1. A method of making a fluorosilicon nitrile compound comprising reacting a chlorosilicon nitrile compound with a fluorinating agent under conditions effective to exchange fluorine atoms for the chlorine atoms in the chlorosilicon nitrile compound and wherein the chlorosilicon nitrile compound has a total of four substituents attached to a silicon atom, wherein one or two of the substituents are chlorine atoms, one or two of the substituents are cyanoalkyl groups, which may be the same as or different from each other, and the remainder of the substituents, if any, are alkyl groups, which are the same as or different from each other.
 2. The method of claim 1, wherein the fluorinating agent is selected from the group consisting of HF, MF, MHF₂ and SbF₃, where M is Na, K, Rb, Cs or NH₄.
 3. The method of claim 1, wherein the chlorosilicon nitrile compound is prepared by hydrosilylation of an alkene with a chloroalkylsilane.
 4. The method of claim 3, wherein the alkene is a cyanoalkene. 